TY - JOUR
T1 - Synthesis and electrochemical behavior of regioisomeric bismethanofullerene derivatives
AU - Xiao, Lixin
AU - Ozawa, Masaki
AU - Iwaya, Mituhiro
AU - Wang, Jian
AU - Shimotani, Hidekazu
AU - Dragoe, Nita
AU - Tanibayashi, Satoru
AU - Kitazawa, Koichi
PY - 2000
Y1 - 2000
N2 - A series of regioisomeric bis-methanofullerenes (diethyl [60]fullerenobisacetate) were prepared by reaction of the sulfonium ylide with C60. Seven stable resultant regioisomers were completely isolated on a preparative HPLC and identified by FT-IR, UV-vis, TOF-MS, and 1H and 13C NMR measurements. The structures of these bisadducts were assigned based on 1) the relationship of the polarities of the regioisomers with the elution order from HPLC; 2) a comparison of their UV-vis spectra with those of corresponding Bingel-Hirsch bisadducts; and 3) the identification of their molecular symmetries by their 1H and 13C NMR spectra. The electrochemical properties of the resultant regioisomeric bismethanofullerene derivatives were investigated through cyclic voltammetry (CV). The bisadducts exhibited more negative reduction potential than the pristine C60. Trans-2- and cis-3- bisadducts had the least negative potential E 1/2 1 of all the other bisadducts.
AB - A series of regioisomeric bis-methanofullerenes (diethyl [60]fullerenobisacetate) were prepared by reaction of the sulfonium ylide with C60. Seven stable resultant regioisomers were completely isolated on a preparative HPLC and identified by FT-IR, UV-vis, TOF-MS, and 1H and 13C NMR measurements. The structures of these bisadducts were assigned based on 1) the relationship of the polarities of the regioisomers with the elution order from HPLC; 2) a comparison of their UV-vis spectra with those of corresponding Bingel-Hirsch bisadducts; and 3) the identification of their molecular symmetries by their 1H and 13C NMR spectra. The electrochemical properties of the resultant regioisomeric bismethanofullerene derivatives were investigated through cyclic voltammetry (CV). The bisadducts exhibited more negative reduction potential than the pristine C60. Trans-2- and cis-3- bisadducts had the least negative potential E 1/2 1 of all the other bisadducts.
UR - http://www.scopus.com/inward/record.url?scp=0033891924&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033891924&partnerID=8YFLogxK
U2 - 10.1080/10641220009351399
DO - 10.1080/10641220009351399
M3 - Article
AN - SCOPUS:0033891924
SN - 1064-122X
VL - 8
SP - 77
EP - 88
JO - Fullerene Science and Technology
JF - Fullerene Science and Technology
IS - 1
ER -